I think my trouble started when we moved to our last home. My kids were in 6th and 8th grade. A cup-de-sac street, in a neighborhood of 3 streets, about 25 homes. It didn't take me long to call my neighbors the Stepford Wives. We lived 2 houses from the T intersection of the cross street where the bus picked the kids up for school. Out they went, everyday, rain or shine. A long line of cars would be parked, with kids waiting, no matter what the weather. When it rained or snowed, my kids would be invited into cars, which they always refused. My younger son rode his bike to school (6 miles) in the spring of 7th and 8th grade. Before that, let's see. I let my older son ride his bike around the block, on the sidewalk, when he was 4, unaccompanied. He walked home from kindergarten (we lived one block behind the school). That was in AZ. My kids played in the woods behind our house when we first moved to MA, and one day, they got lost. They had walkie talkies and I could hear them on the base unit. For some reason the older one left the younger one, and the younger, was probably 6... he found his way out, by me talking him through and looking at landmarks. That did scare me, but I was proud. The next year, DH was supposed to pick him up after school, when he stayed for an activity. My son knew that DH might forget, so before he left for school, he unlocked the back door. When DH didn't show up, he took the late bus home, got in the house, and then followed the protocol we had established. This was before cell phones, so when he called my school, I was already at the school holiday party, quite far away. Then he called my friend, who came over and took him until DH got home. Needless to say, this is the one who became a Marine. They took the train into Boston/Cambridge, alone starting at age 14 or 15, after me showing them how. This really freaked out the other parents. Both started babysitting at age 10-11, after taking the Red Cross class, and they were in demand! We let them stay home alone, for the weekend, when the older one had his license, and we went to NYC, to celebrate our 20th anniversary. Of course, we had our neighbors on alert for any cars parked in front of the house, etc. They were not partiers, anyway.
My kids knew how to cook, clean, handle money and take care of kids by the time they were 18. They had menial jobs in HS, when none of their friends worked. They did their college apps on their own, with our guidance. The fact that they are 33 and 30 and still call for advice, makes me think we did the right thing.